Operated by the Chicago Public Schools (CPS) district, Kenwood opened in temporary quarters in 1966 and in its permanent building in 1969.

[citation needed] In addition to being a neighborhood high school, Kenwood has a city-wide magnet program that accepts students entering into 7th grade who pass a rigorous admissions test.

The magnet program accepts students citywide using a random lottery with a standing of 6 or higher in both reading and math.

With Northern big cities undergoing the final years of the baby boom, the CPS felt the need for a modernized new high school on Chicago's South Side.

Students are offered the choice of staying at Kenwood Academy or attending any other high school with their credits and GPA.

Students that choose to stay at Kenwood are granted the right, in their senior year, to take tuition-free courses at the University of Chicago.

The Kenwood Academy Concert Choir has performed locally and nationally at churches, colleges and universities, and vocal competitions nationwide.

They have also performed for the Annual Hyde Park Jazz Festival, Golden Apple Awards, Ravinia, Hewitt and Associates and Room 43.

[citation needed] Kenwood competes in the Chicago Public League (CPL) and is a member of the Illinois High School Association (IHSA).

The students also wanted a social room in the school to be named in memory of the late Black Panther Party chairman Fred Hampton.

[20] In October 1989, two male students were charged with attempted arson and reckless conduct when they intentionally started a fire at the school.

[21] On October 2, 2003, the body of a newborn baby girl was found in a trash bin at the school by Chicago police officers.